View details for DOI 10.1021/acsinfecdis.6b00106, View details for Web of Science ID 000388161300007. In contrast, exogenous (13)C-labeled N-acetylneuraminic acid ([(13)C]NeuAc) and N-glycolylneuraminic acid (NeuGc) were efficiently incorporated into LOS in a dose-dependent fashion. Previously, we developed isotope-targeted glycoproteomics (IsoTaG) as a mass-independent mass spectrometry method to characterize azide-labeled intact glycopeptides from complex proteomes. The properties of therapeutic proteins can be enhanced by chemical modification. View details for Web of Science ID 000280086800002, View details for PubMedCentralID PMC2907715, View details for DOI 10.1016/j.cplett.2010.04.067, View details for Web of Science ID 000279368000001. The acylated cysteine residues were confirmed by MS. Second, omega-alkynyl-palmitate is preferentially incorporated into transiently expressed H- or N-Ras proteins (but not nonpalmitoylated K-Ras), compared with omega-alkynyl-myristate or omega-alkynyl-stearate, via an alkali sensitive thioester bond. Lee, J. H., Baker, T. J., Mahal, L. K., Zabner, J., Bertozzi, C. R., WIEMER, D. F., Welsh, M. J. Exploiting differences in sialoside expression for selective targeting of MRI contrast reagents. Research on the human pathogen Mycobacterium tuberculosis (Mtb) would benefit from novel tools for regulated gene expression. These modified proteins integrated into the plasma membranes of a variety of mammalian cells and were internalized and directed to recycling endosomes similarly to GFP bearing a native GPI anchor. View details for DOI 10.1074/jbc.M510520200, View details for Web of Science ID 000235426200035. View details for Web of Science ID 000174151500001. Methods for targeting of small molecules to cellular proteins can allow imaging with fluorophores that are smaller, brighter, and more photostable than fluorescent proteins. Bhat, R., Belardi, B., Mori, H., Kuo, P., Tam, A., Hines, W. C., Le, Q., Bertozzi, C. R., Bissell, M. J. Disruption of stf0 in Mycobacterium smegmatis and M. tuberculosis resulted in the loss of T2S and SL-1 formation, respectively. View details for Web of Science ID 000177962200018. Here we report the facile synthesis of a difluorobenzocyclooctyne (DIFBO) that combines these modifications. Northern blot analysis identified a single 5.5-kb ppGalNAc-T transcript. Cell surface reactions of this kind should prove useful in the introduction of new recognition epitopes, such as peptides, oligosaccharides, or small organic molecules, onto cell surfaces and in the subsequent modulation of cell-cell or cell-small molecule binding events. Growth then proceeds by formation of new tetramers exclusively at cluster edges, implying tetramer formation is autocatalytic. We used polymerase chain reaction amplification with degenerate primers and hybridization screening of a T. gondii cDNA library to identify this enzyme. Genomic and proteomic profiling form a basis for biological discovery. These data unambiguously establish the configuration of the resting enzyme metal center and, importantly, reveal the formation of a three-coordinate tris(thiolate) trigonal planar complex upon substrate binding as furthermore supported by density functional theory (DFT) calculations. A critical branch point in mucin-type oligosaccharides is the beta 1-->3 glycosidic linkage to the core alpha-N-acetylgalactosamine (GalNAc) residue. Applications to noninvasive imaging and glycoproteomic analyses are discussed. We designed a 4-N,N-dimethylamino-1,8-naphthalimide-conjugated trehalose (DMN-Tre) probe that undergoes >700-fold increase in fluorescence intensity when transitioned from aqueous to hydrophobic environments. View details for Web of Science ID 000277564700033, View details for PubMedCentralID PMC3035521. Similarly, the ability to perceive the spatial organization of glycans could transform our understanding of their role in development, infection, and disease progression. Moreover, concomitant use of PCL-2 and IETDC in vivo establishes a concurrent increase in both H(2)O(2) and caspase 8 activity during acute inflammation in living mice. The successful integration of living cells into synthetic devices requires precise control over cell patterning. Surprisingly, 6', 6-disulfolactose was poorly recognized by MECA-79, a carbohydrate- and sulfate-dependent monoclonal antibody that binds competitively to L-selectin ligands. Mougous, J. D., Lee, D. H., Hubbard, S. C., Schelle, M. W., Vocadlo, D. J., Berger, J. M., Bertozzi, C. R. An alpha-formylglycine building block for Fmoc-based solid-phase peptide synthesis, Programmable cell adhesion encoded by DNA hybridization. At 60 hours after fertilization, we observed an increase in de novo glycan biosynthesis in the jaw region, pectoral fins, and olfactory organs. The oligonucleotides were introduced using metabolic carbohydrate engineering, which allowed reactive tailoring of the cell surface glycans for chemoselective bioconjugation. To better understand how cell surface oligosaccharides function within their native context, novel chemical approaches to modulating cell surface oligosaccharides structures are now being developed. New developments have allowed researchers to begin probing the inner workings of the cell to gain new insight into cell function and metabolism. The coating layers of macrophages and their targets hinder phagocytosis by both steric and electrostatic means. Wei, W., Riley, N. M., Lyu, X., Bertozzi, C. R., Long, J. Utilizing a biotin-terminated PAH scaffold prepared via RAFT polymerization, we quickly assembled a panel of glycopolymers that we microarrayed on streptavidin-coated glass. Surprisingly, corneas from MyD88-/- mice displayed similar GalNAz labeling to wild-type corneas, but labeling was reduced and patchy on IL-1 receptor (IL-1R)-knockout mouse corneas (P < 0.05, ANOVA). Quantifying and controlling the orientation of surface-bound macromolecules is crucial to a wide range of processes in areas as diverse as biology, materials science, and nanotechnology. Still, glycoconjugate synthesis requires the manipulation of multiple stereocenters and protecting groups and remains the domain of a few expert laboratories around the world. View details for DOI 10.1016/j.chembiol.2004.05.009, View details for Web of Science ID 000222987300018, View details for DOI 10.1002/cbic.200300789, View details for Web of Science ID 000220196800018. A significant proportion (>45%) of the identified O-GlcNAc sites lie in close proximity to or coincide with a known phosphorylation site, supporting the potential for PTM crosstalk. Synthetic Riboswitches That Induce Gene Expression in Diverse Bacterial Species. We developed a multiplex analysis platform based on antibody detection by agglutination-PCR (ADAP) for the sample-sparing measurement of GAD, IA-2 and insulin autoantibodies/antibodies in 1 muL serum. Sulfolipid-1 (SL-1) is an abundant sulfated glycolipid and potential virulence factor found in Mycobacterium tuberculosis. In this study, we describe the development of a high-throughput assay for OGT and use it to profile the specificity of the enzyme among a panel of peptide substrates. We engineered mammalian cells to produce diazirine-modified O-GlcNAc by expressing a mutant form of UDP-GlcNAc pyrophosphorylase and subsequently culturing these cells with a cell-permeable, diazirine-modified form of GlcNAc-1-phosphate. Agard, N. J., Baskin, J. M., Prescher, J. We also found that StcE digests cancer-associated mucins from cultured cells and from ascites fluid derived from patients with ovarian cancer. We provide evidence that conserved switch motifs in the G domain of CysN allosterically mediate interactions between the nucleotide binding sites. Here we investigate the biosynthetic origin of H. ducreyi sialosides by metabolic incorporation studies using a panel of N-acylmannosamine and sialic acid analogues. Metabolic incorporation of d-alanine derivatives and click chemistry detection constitute a facile, modular platform that facilitates unprecedented spatial and temporal resolution of PG dynamics in vivo. Hatzios, S. K., Schelle, M. W., Holsclaw, C. M., Behrens, C. R., Botyanszki, Z., Lin, F. L., Carlson, B. L., Kumar, P., Leary, J. Sulfonucleotide reductases are a diverse family of enzymes that catalyze the first committed step of reductive sulfur assimilation. Diptericin increased the permeability of the outer and inner membranes of Escherichia coli D22 cells, suggesting possible mechanisms of action. We frame central issues regarding determination of protein-level variation and PTMs, including some paradoxes present in the field today. The unique chemical functionality of these analogs is exploited for selective attachment of singlet oxygen-generating fluorescent dyes via bioorthogonal 'click chemistry' ligations. View details for DOI 10.1074/jbc.M313103200, View details for Web of Science ID 000222445300003. Such metabolic interference can block the expression of oligosaccharides or alter the structures of the sugars presented on cells. In addition, GalNAz efficiently labeled mucin-type O-linked glycoproteins expressed at endogenous levels. Natural mucins are densely glycosylated O-linked glycoproteins that serve numerous functions on cell surfaces. [42] Palleon Pharma focuses on investigating glycoimmune checkpoint inhibitors as a potential treatment for cancer. This assembly inhibits L-, E-, and P-selectin binding to GlyCAM-1, a physiological ligand better than sLe(x)-like liposomes without additional anionic charge. These effects were mirrored by expression of the ectodomain of cancer-associated mucin MUC1. We quantified the absolute number of ketone groups displayed on cell surfaces as a function of the concentration of ManLev in the medium. View details for Web of Science ID 000227308100055. The selectins are a family of carbohydrate-binding proteins, or lectins, that have stimulated tremendous interest because of their involvement in a wide array of interactions between leukocytes and endothelial cells. This system provides a platform to study cell-surface phenomena with a degree of chemical control that cannot be achieved using conventional biological tools. Complex aminooxy glycans were synthesized using a new route that features N-pentenoyl hydroxamates as key intermediates that can be readily elaborated chemically and enzymatically. Four recently discovered GlcNAc-6-sulfotransferases are the first candidate contributors to the biosynthesis of 6-sulfo sLex in the context of L-selectin ligands. Varki, A., Cummings, R. D., Aebi, M., Packer, N. H., Seeberger, P. H., Esko, J. D., Stanley, P., Hart, G., Darvill, A., Kinoshita, T., Prestegard, J. J., Schnaar, R. L., Freeze, H. H., Marth, J. D., Bertozzi, C. R., Etzler, M. E., Frank, M., Vliegenthart, J. F., Ltteke, T., Perez, S., Bolton, E., Rudd, P., Paulson, J., Kanehisa, M., Toukach, P., Aoki-Kinoshita, K. F., Dell, A., Narimatsu, H., York, W., Taniguchi, N., Kornfeld, S. Chemistry Is Central to Repairing Genes and Global Health: Reflections on the 2015 Nobel Prizes in Chemistry and Physiology or Medicine. Given that M. tuberculosis typically persists in the phagosomal vacuole after being phagocytosed by macrophages, we performed a proteomic analysis of that organelle after treatment of macrophages with LAMs purified from the two mycobacterial species. However, their diverse structures, which are the key to their function, have hampered studies by biologists and chemists alike. Here, we show that Cu(I)-FGE is functional in O2 activation and reveal a high-resolution X-ray crystal structure of FGE in complex with its catalytic copper cofactor. WebProfessor Carolyn Bertozzi's research interests span the disciplines of chemistry and biology with an emphasis on studies of cell surface sugars important to human health and disease. Their localization was correlated with preferred activity on either N-linked or O-linked glycoproteins. WebBertozzi is a professor of Humanities and Sciences, and of Chemical and Systems Biology and of Radiology. IsoTaG is therefore positioned to enhance structural understanding of the glycoproteome. Mild hydrolysis conditions were established that released sulfated oligosaccharides without cleavage of sulfate esters. This new protocol incorporates 12 known heparin disaccharides, including three sets of isomers. Taken together, these results demonstrate that the active site functionally communicates with the iron-sulfur cluster and also suggest a functional significance for the cysteine dyad in promoting site differentiation within the 4Fe-4S cluster. Several anti-tuberculosis drugs target the biogenesis of this complex envelope, but their efficacy is declining due to resistance. View details for Web of Science ID 000172448800001. The ESI-MS assay is used to determine NodST kinetic parameters, including K(M), V(max), and K(i) (for PAP). Here, we studied the effects of perturbing O-GlcNAcylation during neural induction of hESCs using the metabolic inhibitor of OGT, peracetylated 5-thio-N-acetylglucosamine (Ac4-5SGlcNAc). A., Cheng, E. H., Bertozzi, C. R., Boyce, M. Modulation of Ocular Surface Glycocalyx Barrier Function by a Galectin-3 N-terminal Deletion Mutant and Membrane-Anchored Synthetic Glycopolymers. [reaction: see text]. Wei, W., Riley, N. M., Yang, A. C., Kim, J. T., Terrell, S. M., Li, V. L., Garcia-Contreras, M., Bertozzi, C. R., Long, J. cis-Cyclopropanation of mycobacterial mycolic acids by pcaA drives the activation of host Vegf signaling within granuloma macrophages. Kostiuk, M. A., Corvi, M. M., Keller, B. O., Plummer, G., Prescher, J. This protocol outlines both the generation and the analysis of proteins aldehyde-tagged at their termini and the methods for chemical conjugation to the formylglycine. Advanced microscopy techniques, together with biochemical methods, were used to study the trypomastigote membrane from its glycobiological perspective. Her father, William Bertozzi, was a physics professor at MIT. View details for DOI 10.1016/j.jasms.2006.08.010, View details for Web of Science ID 000244109300001, View details for PubMedCentralID PMC2755055. A., Hangauer, M. J., Bertozzi, C. R., Rajaiah, G., Falck, J. R., Berthiaume, L. G. Synthetic studies toward Mycobacterium tuberculosis sulfolipid-I, Biocompatible carbon nanotubes generated by functionalization with glycodendrimers. We found that substituents on BARAC's aryl rings can alter the calculated transition state interaction energy of the cycloaddition through electronic effects or the calculated distortion energy through steric effects. Within this bilayered structure, registry between lattices in two layers was disclosed, whereas the intrinsic symmetry in each layer was altered. Cross-linked polymethacrylamide and polymethacrylate hydrogels were functionalized with mineral-binding ligands and used to template the formation of hydroxyapatite. The second-order rate constant for PAP was determined to be over 3 orders of magnitude greater than those determined for myo-inositol 1-phosphate (IMP) and fructose 1,6-bisphosphate (FBP), previously considered to be the primary substrates of this enzyme. Barnes, J., Kaushik, S., Bainer, R. O., Sa, J. K., Woods, E. C., Kai, F., Przybyla, L., Lee, M., Lee, H., Tung, J. C., Maller, O., Barrett, A. S., Lu, K. V., Lakins, J. N., Hansen, K. C., Obernier, K., Alvarez-Buylla, A., Bergers, G., Phillips, J. J., Nam, D., Bertozzi, C. R., Weaver, V. M. Glycosyltransferase bump-hole engineering to dissect mucin-type O-glycosylation in the living cell. Here we report that 5'-adenosinephosphosulphate reductase (CysH), an enzyme essential for the production of reduced-sulphur-containing metabolites, is critical for Mycobacterium tuberculosis (Mtb) survival in chronic infection phase in mice. View details for DOI 10.1002/cbic.201000433, View details for Web of Science ID 000286433800014, View details for PubMedCentralID PMC3056122. This function deteriorates during ageing and neurodegenerative disease, concomitant with cognitive decline. Potential for therapeutics and diagnostics, Kinetic measurements and mechanism determination of Stf0 sulfotransferase using mass spectrometry. View details for Web of Science ID 000423267000106, View details for Web of Science ID 000423267000140, View details for DOI 10.1021/acscentsci.7b00540, View details for PubMedCentralID PMC5704282, View details for PubMedCentralID PMC5658776, View details for Web of Science ID 000412089800691, View details for Web of Science ID 000429556701925, View details for Web of Science ID 000429556703083, View details for Web of Science ID 000429556702657, View details for Web of Science ID 000429556702049. Endogenous levels form a basis for biological discovery and inner membranes of Escherichia coli D22,... Advanced microscopy techniques, together with biochemical methods, were used to the! Surprisingly, 6 ', 6-disulfolactose was poorly recognized by MECA-79, a carbohydrate- and sulfate-dependent monoclonal antibody that competitively! 12 known heparin disaccharides, including some paradoxes present in the field today sulfated. 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